


The Sleepover

by CS_impala67



Series: The Sleepover [1]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Blow Jobs, Bottom Dean Winchester, Castiel/Dean Winchester First Time, Coming Out, Dean Winchester Thinks They are Heterosexual, Dean Winchester's First Time With a Man, Gay Castiel (Supernatural), Hand Jobs, M/M, Mildly Dubious Consent, Oral Sex, Painful Sex, Rimming, Top Castiel, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2019-02-19
Updated: 2019-02-19
Packaged: 2019-10-31 18:39:24
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,737
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17854994
Author URL: https://archiveofourown.org/users/CS_impala67/pseuds/CS_impala67
Summary: It started out like any typical sleepover they have had since middle school. Little did Dean know how different this one would turn out.





	1. Part one

**Author's Note:**

> Let me know if there are any tags I have missed!

It was a typical Friday night. Castiel came over Dean’s like he always did on the weekends. It's been a tradition for years. Since jr high, till they graduated a few weeks ago, they hung out every weekend. Neither of them ever had a girlfriend. No one interested Dean and he guessed the same went for Cas. They would rather just hang out together than deal with girls. 

Both boys laid around playing video games and watched a few shows before they decided it was time to sleep. They undressed to their boxers like always and climbed into bed. They always shared a bed so there was nothing weird about it. Dean started to doze off when he felt Cas roll over and face him. He could feel Cas’ breath on his back and it sent shivers down his spine. Then he felt Cas’ hand touch his back and caress it. Now Dean was starting to get weirded out. They may share a bed regularly, but they don’t touch each other. That was definitely crossing a line. 

"what the hell are you doing man?" Dean asked him. Cas jumped.

" Oh, umm I thought you were asleep...I...umm..."

" So you touch me in my sleep!" He yelled.

"I'm sorry. I'm sorry, I don't know why I did it. I'm sorry." is all he could say.

" what's wrong with you.?"

" Listen Dean, I'm sorry. I should have told you but I was afraid." he said, sounding distraught. 

" should have told me what?" Dean asked confused.

" I have a crush on you okay?” He whispered. 

“what did you just say.” He asked stunned. There was no way Dean heard that right. 

“I have a crush on you. I’m gay. I’ve liked you for three years now. And every time we share your bed it kills me not to be able to touch you. I’m sorry I did.”

" Holy shit you gotta be kidding." Dean said stunned. Never in his life would he have thought Cas was gay.

" No, I'm serious. I'm gay. I'm sorry I didn't say anything before but I didn't want you to freak out. I'll go home. I'm sure you don't want me spending the night in your bed now that you know." he said on the verge of tears. 

" No it's okay dude you can stay." Dean said shocking myself. Did he want Cas in his bed? He might try something. Hell he caught Cas touching him already. But for some reason Dean wanted him to stay. 

" You sure you don't mind? I'd understand. I promise I won't try anything with you. I’ll keep my hands to myself"

" It's fine really. Let's just go to sleep." 

Both boys rolled over and fell asleep. The next morning Dean woke up to something poking him in the ass. He reached behind him not thinking and ended up grabbing Castiel's big hard cock. He wasnt expecting that being half asleep. For some reason he didn't let go though. He found myself gripping Cas’ hard cock in his hand and felt myself start to harden. What the hell? 

" You know you should move your hand up and down. I'd like that." He heard Cas sleepily say behind him. He felt his face heat up and quickly removed his hand. 

"Turn around" Cas said.

" No" Dean was too embarrassed to look at him. He got mad at Cas last night for touching his back, and here Dean was practically molesting him in his sleep.

" Please Dean, just look at me." Cas pleaded. Dean turned around but looked down. 

" Dean stop and just look at me." he demanded. Dean looked up at him. Then Cas did something unexpected. He kissed the other boy. Dean felt his lips close on his and instinctively closed his eyes. He bit Dean’s lower lip trying to get him to open his mouth and then he slipped his tongue in. He felt myself moan and then kissed Cas back. Their tongues began to explore each others mouths. Dean never thought he would ever kiss another guy but he was and his cock was rock hard the whole time. 

Castiel broke the kiss first and Dean fell out of my trance.

He felt my face heat up again at the thought of what they just did. He just made out with his best friend...who is a dude. And loved it. 

" Stop being embarrassed Dean." 

" I'm sorry dude but this is all pretty hard to wrap my head around and I can't help being a little embarrassed. I kissed a guy. We just kissed. Don't you feel awkward?" He asked him.

" No I don't. I've been fantasizing about being sexual with you for a few years." he said truthfully.

" You've fantasized about having sex with me?" asked Dean, surprised.

" Yeah. A lot. More than I care to admit."

" What have you fantasized about exactly?"

" I really don't want to give you details. One, because it's embarrassing, and two because I would scare you away." he said.

Now He really wanted to know. Dean was curious about what Cas imagined doing to him . It make his cock hard again with excitement. He didn’t know what was going on with himself or why he was getting excited by a guy but what the hell. If it was feeling good, might as well go with it. 

"what if I said it wouldn't scare my away?" Dean asked.

" Well I have an idea." he said " How about instead of telling you, I show you." 

" Oh...umm...I dunno." 

" Do you trust me?" he asked.

" Yeah of course I do."

" Then let me show you. I promise I'll make you feel good. If you don't like something I'm doing then I'll stop."

" Ok I guess we could try that." 

" Good now lay back and get ready to experience the best time of your life." he said smiling

Dean laid back on the bed and Cas got on top of him. He started kissing Dean again and Dean kissed back full force. His lips then traveled to Dean’s neck and he started sucking and biting on his soft spot. He let out a load moan it felt so good. He then traveled down his neck towards his chest. Then He felt his tongue dart across his nipple and begin licking it.

" uuuuuhhhh ohhhhh" 

" that feel good?" Cas asked. 

"yeah."

Cas continued to lick his nipple and began sucking on it. His teeth then clamped around it and he gently bit down. There was pain but there was also an intense pleasure in it. Dean found himself gripping Cas’ hair and he was driving him wild. As he continued his tongue action Dean felt his hand travel down his body. Starting at his chest, he caressed Dean’s body all the way down his abs till he reached in between his legs and cupped his balls. He gently rubbed them and then brought his hand around Dean’s hard cock, rubbing it through boxers. He needed more. Dean grabbed the waistband of them and started pulling them down while Cas helped. He was then naked on the bed with Cas laying on top of him . Cas grabbed Dean’s cock and he thought he'd died and gone to heaven. No one besides himself had ever touched his cock. The feeling of Cas’ big strong hand around his rock hard member shot pleasure to his toes. His whole body filled with heat and desire. Cas’ lips left his nipples and he began to kiss down the other boy’s chest and abs till he got to his cock. He licked the tip and Dean was going insane. Then he just took his whole cock in his mouth. 

" Oh god Cas. That's amazing!" Dean screamed. He’d never felt pleasure like that. 

" I told you I’m going to make you feel good. We haven't even got started yet." he said and then took Dean’s dick in his mouth again and began bobbing his head up and down sucking and swirling his tongue around his cock. He was in ecstasy. Having Cas’ warm wet mouth making love to his hard cock was amazing. He felt himself slowly building and knew He was close to cumming. 

" Castiel! I'm gonna cum. Get off or I'm gonna..." too late. He couldn't control himself and shot a load right in Cas’ mouth. Cas didn't even move. He sucked his cock dry.

"How did that feel?" he asked, while wiping the cum from his lip.

"Fucking amazing. I've never felt like that before. Maybe I’m not as straight as I thought” Dean said chuckling breathlessly. 

"Just wait. We are only beginning. Now roll over and let me show you more" 

......to be continued.......


	2. Part two

"Just wait. We are only beginning. Now roll over and let me show you more" 

Dean did as he was told. He was nervous and excited all at the same time. Castiel climbed on top of his back, naked as well. He started kissing Dean’s neck and grinding himself on Dean . He could feel Cas’ hard cock rubbing up and down in the crack of his ass and it filled him with anticipation. Cas slowly started kissing down Dean’s back till he got to the top of his ass. His hands grabbed Dean’s round cheeks and pulled them apart. 

" You have such a sexy ass Dean." he said. " I've always wanted to touch it." 

The next thing Dean felt shocked the hell out of him. He felt something warm and wet touch his hole and realized Cas was licking his asshole. It felt weird but amazing at the same time. 

" Oh Cas!" He moaned.

" You like that Dean ?" 

" oh god yes!!!" 

" I'm gonna tongue fuck you." Cas said and then Dean felt him push his wet tongue into his ass. He almost screamed. Dean didn't realize how sensitive he was there and as Cas’ tongue moved in and out of his tight ass, it brought him so much pleasure. He grabbed the sheets trying not to flop around at the insane pleasure he was bringing Dean. In and out, he felt Cas’ tongue move in his ass. He never wanted it to end. All of a sudden he felt Cas remove his tongue and then felt a finger press against his hole. He started to panic.

" Hey what are you doing?" He asked Cas worried.

" Just trust me." Cas replied. 

" Man I don't know. This is too much." Dean replied.

" Do you want me to make you feel good? " 

" Umm yeah."

" Then trust me. Be open minded. I told you if you don't like something I'm doing I will stop, but at least try it first." he said as he rubbed Dean’ back.

" Okay. " 

" Okay just relax. I'm gonna make you feel good. This will feel weird at first but then it feels so good." 

Dean felt Cas place his finger against his hole again as he rubbed it. He felt the pressure of him pushing his finger into his entrance. He broke through and slowly pushed in all the way. Dean yelped. It hurt but he didn't tell him to stop. He wanted to see why he said it was going to feel good. He felt him pull his finger back and slowly push back in. He did this again and again. Dean was about to tell him he didn't like it when he felt something and screamed. 

" UUUUHHHHHH!!! OH MY FREAKING GOD!!!" He yelled.

" What? Did I hurt you?" Cas asked worried. 

 

" Hell no!!!! What did you just hit? That was the most amazing thing I've ever felt!!!"

" Oh I hit your prostate. It's the male G Spot." Cas said and then pushed his finger in Dean again hitting that same spot. 

" UH OH GOD DON'T STOP!!!"

He fingered Dean again and again hitting his prostate over and over driving him crazy. He was in a euphoric state. The pleasure was like nothing he’d ever felt before. He wasn't thinking straight (pun intended)”

 

" OH GOD CASTIEL. I WANT YOU INSIDE ME!" Dean screamed, shocking both of them making them jump apart. 

" Oh umm. I can't believe I just said that." Dean mumbled completely embarrassed, hiding his hands in front of his face. 

" Dean look at me." Cas said. 

Dean slowly lifted his head to look at Cas, his face read from embarrassment.

" What did I tell you about being embarrassed. Stop it. I will never judge you” Cas said.

 

" I just screamed for you to basically fuck me. I've always thought I was straight until today and I just asked you to fuck me. Of course I'm embarrassed." Dean said. 

 

" Listen. You didn't know what you were saying. It was the heat of the moment. You couldn't help it."

" But see thats the point. I wasn't thinking clearly so I was speaking my mind without thought. So obviously what I said was what I was thinking!"

" Dean. Do you want me to fuck you?"

" Umm... I think I do. But now I'm nervous about it. But you were making me feel so good. But now I'm freaking out and over thinking it. What if it hurts?"

 

" Stop over thinking it. I'm not gonna fuck you." 

" Why not?"

" Because I'm gonna make love to you instead." 

" Umm okay. But just uh...be gentle." Dean said nervously.

Dean laid back on the bed and Cas got in between his legs. He leaned on top of Dean and started kissing him. He aligned his cock with Dean’s entrance and start to slowly push into him. He felt Cas’ cock break through his hole and it hurt. 

" It hurts take it out." He said as tears filled my eyes. 

" If you want me to pull out I will. But I promise if I continue it will feel better. It always hurts at first."

" okay just go real slow" Dean said not really wanting him to continue. It hurt so freaking bad he wanted to scream but he also didn’t want Cas to think he was a wimp. He just hoped he was able to take it all. Only the head was in and it hurt. He felt Cas push in a little more. His cock was stretching his hole so much it was tearing it. He held it there and let Dean get used to it and then slowly pushed some more in. Then one last thrust and Dean felt Cas’ balls touch his ass. He knew he was all the way in. Dean was fighting back tears. Cas kissed his eyes and then his lips landed on Dean’s . He kissed him so passionately it took his mind off of the pain a little. He took his chance to pull out slightly and then push back in.

“Uh you are so tight Dean . Your ass is griping my cock so good I love it.”  Cas moaned.

He started pulling out and thrusting back in, very slowly so as not to hurt Dean much. It hurt but he could feel his hole slowly adjust to it. The pain started to subside and it actually started to feel good. 

“Cas” He said

“Yeah Dean?” Cas said as he was slowly thrusting into Dean.

“Do you think you could…umm… go a little faster” Dean said, blushing red.

“You want me to go faster?” 

“Oh god yes its feeling so good.”

Cas started to increase his thrusts into Dean. He pulled all the way out and thrust hard.

“Oh god you hit the spot don’t stop?” Dean moaned

Cas began thrusting hard into him, hitting Dean’s prostate causing him to see stars. He was in fucking heaven.

“Oh Castiel! fuck me harder” Dean lost complete control of his body, of his mind.

“Oh I’ll fuck you harder baby.” Cas yelled as he began pounding his hard cock into Dean’s tight ass. Fast and hard he banged him, his balls slapping Dean’s ass every time he thrust into him. 

“Oh God Cas don’t stop. Yeah that feels so good. Fuck me good.” Dean yelled.

He was fucking Dean so hard. Hitting his prostate every time. All of a sudden, Dean felt his cock shooting between them.

“Uhhhhhhhhh I Love you Dean” Castiel moaned as Dean felt him fill his hole with his hot cum.

Cas collapsed on top of Dean, both of them breathing hard.

Then it registered what he just said. And Dean yelled, You What?!?!” 

 

……….To Be Continued………..

**Author's Note:**

> I have tagged this mildly dubious consent for two reasons. One is because Castiel touches Dean’s back when he thinks he is sleeping. Two, Dean touches Castiel’s penis while half asleep. Cas actually wants it though and Dean ends up being fine with everything. I tagged just in case though.
> 
>  
> 
> Also, this is completely written, I just need to edit it before I put up the other chapter and rest of series.


End file.
